Dyeing process



United StatesPatentO 2,989,361 DYEING PROCESS Walter Hees, Koln-Hohenberg, Germany, assignor to Farbenfabriken Bayer Aktiengesellschaft, Leverkusen,

Germany, a corporation of Germany 1 No Drawing. Filed Aug. 5, 1958, Ser. No. 753,201

Claims priority, application Germany Aug. 14, 1957 6 Claims. (Cl. 8-55) The present invention relates to a dyeing process; more particularly it concerns a process wherein articles of polyacrylonitrile, polyvinylidene-cyanide or co-polymers thereof with other vinyl compounds, are dyed with cationic dyestuffs in the presence of quaternary ammonium compounds containing a benzyl radical which may be substituted by halogen, and an alkyl radical having at least 8 carbon atoms. By the presence of the quaternary ammonium compounds the dyeing is effected in an excellent levelness.

Suitable quaternary ammonium compounds are for example those which derive from fatty amines containing 8 to 18, preferably 12 to 16, carbon atoms, and are obtainable therefrom by the introduction of low molecular weight alkyl radicals such as methyl groups, and by the subsequent reaction with benzyl chloride or 3,4-dichlorobenzyl chloride.

It has moreover been found that especially advantageous results are achieved by using the quaternary ammonium compounds in the form of their addition products with urea or urea derivatives such as monoacetyl urea. Such addition products are obtainable for example by melting the quaternary ammonium compounds with urea or urea derivatives.

The amount of the quaternary compounds or their urea addition products required in each case may easily be ascertained by preliminary tests; detailed explanations will be found in the following examples.

Cationic dyestuffs which are suitable for the dyeing of articles from polyacrylonitrile, polyvinylidene-cyanide or co-polymers thereof with other vinyl compounds, are described for example in American Dyestuif Reporter 1954, pages 432433.

The process of the invention enables articles produced from the aforesaid polymers such as filaments, fibres, fabrics and foils to be dyed with cationic dyestuffs substantially more level than would be possible in the presence of the hitherto proposed levelling agents.

The following examples serve to illustrate the invention without, however, limiting the scope thereof.

Example 1 Yarns of polyacrylonitrile fibres are introduced at 50 C. into a dyebath containing per litre 0.05 gram of the cationic dyestufi 0.2. gram of dimethyl-cetyl-benzyl-ammonium chloride, 0.25 gram of sodium acetate and 0.2 gram of glacial acetic acid, using a liquor-to-goods ratio of 40:1. The temperatures of the liquor is slowly raised from 50 C. to 9698 C. and the dyebath is kept at this temperature for 1 hour. A pale pink dyeing of excellent levelness is obtained.

Example 2 A fabric of polyacrylonitrile filaments is introduced 2,989,361 Patented June 20, 1961 ICC 2 into 'a bath containing per litre 0.1 gram of the cationic dyestulf 0.15 gram of the quaternary ammonium compound obtainable by reaction of dimethyl palm kernel fatty amine with benzyl chloride, 0.2 gram of sodium acetate and 0.3 gram of glacial acetic acid, using a liquor-to-goods ratio of 40:1. The dyeing is started at 60 C., the temperature is slowly raised to 98 C. and the dyeing is completed at this temperature within 1 hour. An excellently level lemon-yellow dyeing is thus obtained.

Example 3 Polyacrylonitrile fibres are introduced into a bath containing per litre 0.125 gram of the cationic dyestufif Example 4 A fabric from polyacrylonitrile fibres is introduced at 60 C. into a bath containing per litre 0.1 gram of the cationic dyestuif of Example 1, 0.3 g. of the addition product described below, 0.3 gram of sodium acetate and 0.3 gram of glacial acetic acid, using a liquor-togoods ratio of 40:1. The temperature of the liquor is slowly raised from 60 to 98 C. and the bath is kept at this temperature for about 9 0 minutes. A completely level pink dyeing is obtained.

The addition product employed is obtainable by melting 30 parts by weight of the quaternary ammonium compound, prepared by reacting dimethyl-palmkernel fatty amine with benzyl chloride, together with 55 parts by weight of urea and 15 parts by weight of monoacetyl urea.

I claim:

1. In the process for dyeing articles produced from a member selected from the group consisting of polyacrylonitrile, polyvinylidene-cyanide and copolymers thereof with other vinyl compounds, the improvement which comprises applying onto said articles, as leveling agent, a quaternary ammonium compound containing attached to the nitrogen atom an alkyl radical of at least 8 carbon atoms, and a radical selected from the group consisting of benzyl and halogenated benzyl.

2. A process according to claim 1 which comprises applying said quaternary ammonium compound in form of its reaction product with a compound selected from the group consisting of urea and derivatives of urea.

3. A process of claim 1 wherein the quaternary ammonium compound is dimethyl-cetyl-benzyl-ammonium chloride.

4. A process of claim 1 wherein the quaternary ammonium compound is the reaction product of dimethylpalm-kernel fatty amine with benzyl chloride.

5. A process of claim 1 wherein the leveling agent is the addition product of dimethyl-cetyl-benzyl-ammonium chloride, urea and monoacetyl urea.

6. A process of claim 1 wherein the leveling agent is the addition product obtained by melting urea, monoacetyl urea and a quaternary ammonium compound obtained by reacting dimethyl-palmkernel fatty amine with benzyl chloride.

References Cited in the file of this patent Man-Made Textiles, December 1955, pp. 67-68.

Diserens: The Chem. Tech. of Dyeing and Printing, vol. II, Reinhold Pub. Corp., N.Y., 1951, pp. 108, 327- 328.

Venkataraman: The Chem. of Synthetic Dyes, Academic Press Inc., 1952, N.Y., pp. 295, 879. 

1. IN THE PROCESS FOR DYEING ARTICLES PRODUCED FROM A MEMBER SELECTED FROM THE GROUP CONSISTING OF POLYACRYLONITRILE, POLYVINYLIDENE-CYANIDE AND COPOLYMERS THEREOF WITH OTHER VINYL COMPOUNDS, THE IMPROVEMENT WHICH COMPRISES APPLYING ONTO SAID ARTICLES, AS LEVELING AGENT, A QUATERNARY AMMONIUM COMPOUND CONTAINING ATTACHED TO THE NITROGEN ATOM AN ALKYL RADICAL OF AT LEAST 8 CARBON ATOMS, AND A RADICAL SELECTED FROM THE GROUP CONSISTING OF BENZYL AND HALOGENATED BENZYL. 